Allyl Alcohol → 6-Chloro-2-phenylmethoxy-4-(2-propenyloxy)pyrimidine

HRID 1449438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449438
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH2:17]([OH:20])[CH:18]=[CH2:19].[H-].[Na+]>CN(C)C=O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=[C:2]([O:20][CH2:17][CH:18]=[CH2:19])[CH:7]=1

Komponenten

5

Edukt 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 196938984,6-Dichloro-2-(phenylmethoxy)pyrimidine

Produkt 1

HCID 196938826-Chloro-2-phenylmethoxy-4-(2-propenyloxy)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4,6-Dichloro-2-(phenylmethoxy)pyrimidine (Compound I-173) (1.5 g, 5.9 mmol) and allyl alcohol (0.342 g, 5.9×1.0 mmol) were introduced into a 50 ml eggplant type flask, to which dimethylformamide (20 ml) was added to form a solution. While cooling with ice, 60% sodium hydride (0.247 g, 5.9×1.05 mmol) which had been washed with hexane was added. After stirred for one night at room temperature, the reaction solution was poured into iced water and extracted with toluene (40 ml). The organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and thereafter, the solvent was distilled off to afford an oily product, which was then purified on silica gel column chromatography (Wakogel C300, 300 ml, hexane/ethyl acetate=25/1000(v/v)) to obtain the compound (I-343).

Aufarbeitung

  1. additionwas added
  2. customto form a solution
  3. washhad been washed with hexane
  4. additionwas added
  5. additionthe reaction solution was poured into iced water
  6. extractionextracted with toluene (40 ml)
  7. washThe organic phase was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off
  10. customto afford an oily product, which
  11. customwas then purified on silica gel column chromatography (Wakogel C300, 300 ml, hexane/ethyl acetate=25/1000(v/v))
  12. customto obtain the compound (I-343)

Quellen und Nachweise

ORD-Eintrag
ord-3266352ec5474fa5bf2757fac2b8a492
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599770

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